NPASS Compound

Structure

NPC260886 OpenBabel07101719512D 42 45 0 0 1 0 0 0 0 0999 V2000 -0.4617 2.7126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3081 4.1785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1900 3.4380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6889 1.8206 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2309 -2.7462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9235 -2.7462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0544 2.2240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5658 3.0703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6726 0.0046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0079 -0.7118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9994 -0.4149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0497 -0.6452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2749 0.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3754 0.0622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6007 1.2301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3846 4.1785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0387 2.1972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0772 -1.2803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2309 3.6899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8213 1.2445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2309 -0.7917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3846 2.2240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3352 1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4617 3.6899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9726 2.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0772 -2.2576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6509 0.9998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2309 2.7126 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8874 0.9564 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2309 0.1855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9767 1.7072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9096 0.5124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5522 0.5124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2309 0.7582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0772 2.2240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7198 0.2220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3846 1.2468 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0772 1.2468 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2522 2.6448 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6736 -0.0969 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2309 -0.2191 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 7 35 1 0 0 0 0 8 35 1 0 0 0 0 9 36 1 0 0 0 0 10 36 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 2 0 0 0 0 14 27 2 0 0 0 0 15 27 1 0 0 0 0 16 19 1 0 0 0 0 16 24 2 0 0 0 0 17 20 1 0 0 0 0 17 25 2 0 0 0 0 18 21 1 0 0 0 0 18 26 2 0 0 0 0 21 30 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 23 37 1 0 0 0 0 27 31 1 0 0 0 0 28 19 1 1 0 0 0 28 35 1 0 0 0 0 29 20 1 1 0 0 0 29 36 1 0 0 0 0 30 32 1 0 0 0 0 30 33 2 0 0 0 0 31 39 2 0 0 0 0 32 38 1 0 0 0 0 32 40 2 0 0 0 0 33 37 1 0 0 0 0 33 42 1 0 0 0 0 34 37 1 0 0 0 0 34 38 1 0 0 0 0 34 41 2 0 0 0 0 35 38 1 0 0 0 0 36 42 1 0 0 0 0 37 22 1 1 0 0 0 38 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.37
Volume:	640.374
LogP:	9.725
LogD:	6.781
LogS:	-5.726
# Rotatable Bonds:	8
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.178
Synthetic Accessibility Score:	6.044
Fsp3:	0.553
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.973
MDCK Permeability:	1.998584957618732e-05
Pgp-inhibitor:	0.044
Pgp-substrate:	0.182
Human Intestinal Absorption (HIA):	0.094
20% Bioavailability (F20%):	0.842
30% Bioavailability (F30%):	0.938

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.095
Plasma Protein Binding (PPB):	88.45685577392578%
Volume Distribution (VD):	2.664
Pgp-substrate:	7.99466609954834%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.635
CYP2C19-substrate:	0.829
CYP2C9-inhibitor:	0.888
CYP2C9-substrate:	0.176
CYP2D6-inhibitor:	0.398
CYP2D6-substrate:	0.015
CYP3A4-inhibitor:	0.896
CYP3A4-substrate:	0.898

ADMET: Excretion

Clearance (CL):	15.369
Half-life (T1/2):	0.005

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.964
Drug-inuced Liver Injury (DILI):	0.897
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.452
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.662
Carcinogencity:	0.353
Eye Corrosion:	0.004
Eye Irritation:	0.027
Respiratory Toxicity:	0.983

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC260886

Natural Product ID:	NPC260886
*Common Name:**	Garcimultiflorone A
IUPAC Name:	n.a.
Synonyms:	Garcimultiflorone A
Standard InCHIKey:	CENBILPUSBONJA-DORJWPPLSA-N
Standard InCHI:	InChI=1S/C38H50O4/c1-24(2)16-19-28-22-37-23-29(20-17-25(3)4)36(9,10)42-33(37)30(21-18-26(5)6)32(40)38(34(37)41,35(28,7)8)31(39)27-14-12-11-13-15-27/h11-18,28-29H,19-23H2,1-10H3/t28-,29+,37+,38+/m1/s1
SMILES:	CC(=CC[C@@H]1C[C@]23C[C@H](CC=C(C)C)C(C)(C)OC2=C(CC=C(C)C)C(=O)[C@@](C(=O)c2ccccc2)(C3=O)C1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558953
PubChem CID:	25243253
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33077	garcinina multiflora	Species	n.a.	n.a.	fruits	n.a.	n.a.	PMID[19203247]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
GI50	2
IC50	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	GI50	=	24800.0	nM	PMID[527356]
NPT1086	Cell Line	SK-HEP1	Homo sapiens	GI50	>	30000.0	nM	PMID[527356]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	5580.0	nM	PMID[527355]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4650.0	nM	PMID[527355]
NPT2	Others	Unspecified		IC50	=	16500.0	nM	PMID[527356]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC260886 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	1358
0.2-0.3	2370
0.3-0.4	7699
0.4-0.5	14490
0.5-0.6	13295
0.6-0.7	2892
0.7-0.8	223
0.8-0.85	23
0.85-0.9	20
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9817	High Similarity	NPC268930
0.9115	High Similarity	NPC61651
0.9091	High Similarity	NPC218855
0.906	High Similarity	NPC325740
0.9043	High Similarity	NPC476225
0.8929	High Similarity	NPC130591
0.8929	High Similarity	NPC234637
0.8839	High Similarity	NPC471481
0.875	High Similarity	NPC294050
0.875	High Similarity	NPC328997
0.8678	High Similarity	NPC146239
0.8607	High Similarity	NPC316553
0.8361	Intermediate Similarity	NPC472693
0.8361	Intermediate Similarity	NPC472694
0.8276	Intermediate Similarity	NPC294458
0.8268	Intermediate Similarity	NPC144257
0.8235	Intermediate Similarity	NPC472697
0.8235	Intermediate Similarity	NPC472698
0.823	Intermediate Similarity	NPC470007
0.8198	Intermediate Similarity	NPC471829
0.8198	Intermediate Similarity	NPC474866
0.8198	Intermediate Similarity	NPC472691
0.8198	Intermediate Similarity	NPC475939
0.819	Intermediate Similarity	NPC477475
0.819	Intermediate Similarity	NPC477476
0.8175	Intermediate Similarity	NPC471832
0.812	Intermediate Similarity	NPC326664
0.808	Intermediate Similarity	NPC470648
0.8065	Intermediate Similarity	NPC478108
0.8033	Intermediate Similarity	NPC476234
0.8016	Intermediate Similarity	NPC472678
0.8	Intermediate Similarity	NPC192577
0.7984	Intermediate Similarity	NPC328107
0.7984	Intermediate Similarity	NPC472681
0.7969	Intermediate Similarity	NPC472692
0.7969	Intermediate Similarity	NPC471334
0.7969	Intermediate Similarity	NPC472682
0.7955	Intermediate Similarity	NPC118366
0.7949	Intermediate Similarity	NPC280789
0.7937	Intermediate Similarity	NPC48992
0.7909	Intermediate Similarity	NPC239185
0.7899	Intermediate Similarity	NPC215419
0.7881	Intermediate Similarity	NPC470253
0.7881	Intermediate Similarity	NPC143768
0.7876	Intermediate Similarity	NPC247976
0.7869	Intermediate Similarity	NPC202015
0.7863	Intermediate Similarity	NPC137315
0.7863	Intermediate Similarity	NPC265513
0.7857	Intermediate Similarity	NPC476993
0.7851	Intermediate Similarity	NPC94425
0.7838	Intermediate Similarity	NPC134882
0.7826	Intermediate Similarity	NPC100767
0.781	Intermediate Similarity	NPC294679
0.781	Intermediate Similarity	NPC144247
0.781	Intermediate Similarity	NPC8493
0.781	Intermediate Similarity	NPC469375
0.781	Intermediate Similarity	NPC145301
0.7805	Intermediate Similarity	NPC472679
0.7805	Intermediate Similarity	NPC232958
0.7805	Intermediate Similarity	NPC472680
0.7797	Intermediate Similarity	NPC292834
0.7768	Intermediate Similarity	NPC54647
0.7768	Intermediate Similarity	NPC476042
0.7759	Intermediate Similarity	NPC472683
0.7759	Intermediate Similarity	NPC472701
0.7759	Intermediate Similarity	NPC472696
0.7759	Intermediate Similarity	NPC472695
0.7752	Intermediate Similarity	NPC25736
0.7748	Intermediate Similarity	NPC265220
0.7731	Intermediate Similarity	NPC93287
0.7706	Intermediate Similarity	NPC59677
0.7706	Intermediate Similarity	NPC1682
0.7706	Intermediate Similarity	NPC188844
0.7705	Intermediate Similarity	NPC222968
0.7705	Intermediate Similarity	NPC80605
0.7705	Intermediate Similarity	NPC323440
0.7699	Intermediate Similarity	NPC109514
0.7698	Intermediate Similarity	NPC318067
0.7679	Intermediate Similarity	NPC145052
0.7679	Intermediate Similarity	NPC75724
0.7672	Intermediate Similarity	NPC472700
0.7672	Intermediate Similarity	NPC472699
0.7667	Intermediate Similarity	NPC67377
0.7667	Intermediate Similarity	NPC241851
0.7661	Intermediate Similarity	NPC238861
0.7661	Intermediate Similarity	NPC77000
0.7661	Intermediate Similarity	NPC475804
0.7661	Intermediate Similarity	NPC474222
0.7658	Intermediate Similarity	NPC219573
0.7658	Intermediate Similarity	NPC185208
0.7652	Intermediate Similarity	NPC329282
0.7647	Intermediate Similarity	NPC212415
0.7623	Intermediate Similarity	NPC469843
0.7619	Intermediate Similarity	NPC65627
0.7615	Intermediate Similarity	NPC284475
0.7607	Intermediate Similarity	NPC203732
0.7603	Intermediate Similarity	NPC474095
0.7597	Intermediate Similarity	NPC115797
0.7597	Intermediate Similarity	NPC51448
0.7597	Intermediate Similarity	NPC268607
0.7589	Intermediate Similarity	NPC240042
0.7578	Intermediate Similarity	NPC478107
0.7578	Intermediate Similarity	NPC470649
0.7568	Intermediate Similarity	NPC260233
0.7563	Intermediate Similarity	NPC291799
0.7561	Intermediate Similarity	NPC152812
0.7559	Intermediate Similarity	NPC51079
0.7559	Intermediate Similarity	NPC85511
0.7545	Intermediate Similarity	NPC153885
0.7545	Intermediate Similarity	NPC323420
0.7542	Intermediate Similarity	NPC470252
0.7541	Intermediate Similarity	NPC62138
0.7541	Intermediate Similarity	NPC135730
0.754	Intermediate Similarity	NPC167323
0.754	Intermediate Similarity	NPC269923
0.7522	Intermediate Similarity	NPC49994
0.7521	Intermediate Similarity	NPC196075
0.7521	Intermediate Similarity	NPC471721
0.752	Intermediate Similarity	NPC474223
0.752	Intermediate Similarity	NPC475827
0.7519	Intermediate Similarity	NPC474106
0.75	Intermediate Similarity	NPC318173
0.7481	Intermediate Similarity	NPC7464
0.748	Intermediate Similarity	NPC474254
0.748	Intermediate Similarity	NPC474159
0.7477	Intermediate Similarity	NPC238219
0.7465	Intermediate Similarity	NPC46549
0.7465	Intermediate Similarity	NPC264229
0.7462	Intermediate Similarity	NPC478165
0.7462	Intermediate Similarity	NPC478162
0.746	Intermediate Similarity	NPC472981
0.746	Intermediate Similarity	NPC144547
0.7455	Intermediate Similarity	NPC133461
0.7447	Intermediate Similarity	NPC273798
0.7445	Intermediate Similarity	NPC294330
0.7444	Intermediate Similarity	NPC472656
0.7442	Intermediate Similarity	NPC470765
0.744	Intermediate Similarity	NPC204784
0.7438	Intermediate Similarity	NPC469547
0.7434	Intermediate Similarity	NPC278228
0.7434	Intermediate Similarity	NPC103048
0.7414	Intermediate Similarity	NPC274443
0.7398	Intermediate Similarity	NPC226093
0.7391	Intermediate Similarity	NPC112552
0.7387	Intermediate Similarity	NPC155232
0.7385	Intermediate Similarity	NPC470753
0.7385	Intermediate Similarity	NPC51292
0.7385	Intermediate Similarity	NPC473220
0.7381	Intermediate Similarity	NPC988
0.7381	Intermediate Similarity	NPC289432
0.7381	Intermediate Similarity	NPC105709
0.7372	Intermediate Similarity	NPC165191
0.7372	Intermediate Similarity	NPC50615
0.7372	Intermediate Similarity	NPC473779
0.7372	Intermediate Similarity	NPC46242
0.7372	Intermediate Similarity	NPC473479
0.7372	Intermediate Similarity	NPC289358
0.7372	Intermediate Similarity	NPC5014
0.7372	Intermediate Similarity	NPC477849
0.7372	Intermediate Similarity	NPC114333
0.7372	Intermediate Similarity	NPC469857
0.7372	Intermediate Similarity	NPC149773
0.7372	Intermediate Similarity	NPC28592
0.7372	Intermediate Similarity	NPC91887
0.7372	Intermediate Similarity	NPC23667
0.7372	Intermediate Similarity	NPC245760
0.7372	Intermediate Similarity	NPC51531
0.7372	Intermediate Similarity	NPC157284
0.7372	Intermediate Similarity	NPC42384
0.7372	Intermediate Similarity	NPC297797
0.7368	Intermediate Similarity	NPC476120
0.7368	Intermediate Similarity	NPC271475
0.7364	Intermediate Similarity	NPC295664
0.7355	Intermediate Similarity	NPC186128
0.7348	Intermediate Similarity	NPC262819
0.7345	Intermediate Similarity	NPC12695
0.7343	Intermediate Similarity	NPC132810
0.7339	Intermediate Similarity	NPC157778
0.7333	Intermediate Similarity	NPC23894
0.7329	Intermediate Similarity	NPC305710
0.7328	Intermediate Similarity	NPC244427
0.7328	Intermediate Similarity	NPC222390
0.7317	Intermediate Similarity	NPC470764
0.7317	Intermediate Similarity	NPC228936
0.7317	Intermediate Similarity	NPC217111
0.7304	Intermediate Similarity	NPC221825
0.7302	Intermediate Similarity	NPC476645
0.7288	Intermediate Similarity	NPC134120
0.7288	Intermediate Similarity	NPC172483
0.7281	Intermediate Similarity	NPC226041
0.7273	Intermediate Similarity	NPC474057
0.7266	Intermediate Similarity	NPC473527
0.7265	Intermediate Similarity	NPC329556
0.7259	Intermediate Similarity	NPC203486
0.7259	Intermediate Similarity	NPC126516
0.7259	Intermediate Similarity	NPC329913
0.7258	Intermediate Similarity	NPC471616
0.7257	Intermediate Similarity	NPC472880
0.7252	Intermediate Similarity	NPC81135
0.7252	Intermediate Similarity	NPC473423

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC260886 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	877
0.2-0.3	1291
0.3-0.4	3209
0.4-0.5	2305
0.5-0.6	1033
0.6-0.7	112
0.7-0.8	12
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7909	Intermediate Similarity	NPD3495	Discontinued
0.7886	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD6858	Approved
0.7731	Intermediate Similarity	NPD7094	Approved
0.7706	Intermediate Similarity	NPD7631	Approved
0.7705	Intermediate Similarity	NPD7610	Discontinued
0.7661	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7009	Phase 2
0.7615	Intermediate Similarity	NPD7609	Phase 3
0.7563	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7961	Discontinued
0.7265	Intermediate Similarity	NPD1930	Approved
0.7265	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD1929	Approved
0.7248	Intermediate Similarity	NPD650	Approved
0.7168	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD2066	Phase 3
0.712	Intermediate Similarity	NPD3317	Approved
0.7107	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD3972	Approved
0.7059	Intermediate Similarity	NPD5909	Discontinued
0.7054	Intermediate Similarity	NPD4879	Approved
0.704	Intermediate Similarity	NPD5951	Approved
0.7034	Intermediate Similarity	NPD1932	Approved
0.6993	Remote Similarity	NPD7236	Approved
0.6977	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD2329	Discontinued
0.694	Remote Similarity	NPD7084	Phase 3
0.693	Remote Similarity	NPD1508	Approved
0.6889	Remote Similarity	NPD7055	Discontinued
0.6852	Remote Similarity	NPD942	Approved
0.6825	Remote Similarity	NPD6010	Discontinued
0.6818	Remote Similarity	NPD4878	Approved
0.6757	Remote Similarity	NPD7239	Suspended
0.6752	Remote Similarity	NPD1989	Approved
0.6752	Remote Similarity	NPD1843	Approved
0.6742	Remote Similarity	NPD6287	Discontinued
0.6741	Remote Similarity	NPD2798	Approved
0.6739	Remote Similarity	NPD7713	Phase 3
0.6723	Remote Similarity	NPD7798	Approved
0.6715	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2346	Discontinued
0.6643	Remote Similarity	NPD1471	Phase 3
0.6641	Remote Similarity	NPD3024	Approved
0.6641	Remote Similarity	NPD3025	Approved
0.664	Remote Similarity	NPD1317	Discontinued
0.6638	Remote Similarity	NPD1088	Approved
0.6637	Remote Similarity	NPD3573	Approved
0.6637	Remote Similarity	NPD1087	Approved
0.6621	Remote Similarity	NPD8166	Discontinued
0.6609	Remote Similarity	NPD3673	Approved
0.6609	Remote Similarity	NPD3672	Approved
0.6594	Remote Similarity	NPD7008	Discontinued
0.6593	Remote Similarity	NPD1876	Approved
0.6591	Remote Similarity	NPD2932	Approved
0.6587	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.656	Remote Similarity	NPD2182	Approved
0.6557	Remote Similarity	NPD6647	Phase 2
0.6547	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD1470	Approved
0.6541	Remote Similarity	NPD3026	Approved
0.6541	Remote Similarity	NPD3023	Approved
0.6528	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD1693	Approved
0.6515	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD2799	Discontinued
0.65	Remote Similarity	NPD8032	Phase 2
0.6493	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD1201	Approved
0.649	Remote Similarity	NPD7458	Discontinued
0.6475	Remote Similarity	NPD2193	Phase 2
0.6475	Remote Similarity	NPD2648	Phase 3
0.6466	Remote Similarity	NPD1089	Approved
0.6466	Remote Similarity	NPD1086	Approved
0.6466	Remote Similarity	NPD3019	Approved
0.6466	Remote Similarity	NPD1090	Approved
0.6455	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6637	Approved
0.6441	Remote Similarity	NPD1202	Approved
0.6441	Remote Similarity	NPD1563	Approved
0.6429	Remote Similarity	NPD2313	Discontinued
0.6429	Remote Similarity	NPD7819	Suspended
0.6419	Remote Similarity	NPD3300	Phase 2
0.6398	Remote Similarity	NPD7799	Discontinued
0.6395	Remote Similarity	NPD7003	Approved
0.6387	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD2629	Approved
0.6385	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5346	Phase 2
0.6379	Remote Similarity	NPD800	Approved
0.6379	Remote Similarity	NPD5347	Phase 2
0.6378	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD164	Approved
0.6371	Remote Similarity	NPD1237	Approved
0.635	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7057	Phase 3
0.6346	Remote Similarity	NPD7058	Phase 2
0.6345	Remote Similarity	NPD6099	Approved
0.6345	Remote Similarity	NPD2796	Approved
0.6345	Remote Similarity	NPD6100	Approved
0.6343	Remote Similarity	NPD5836	Discontinued
0.6343	Remote Similarity	NPD2345	Approved
0.6333	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.632	Remote Similarity	NPD5048	Discontinued
0.6311	Remote Similarity	NPD1238	Approved
0.6301	Remote Similarity	NPD2344	Approved
0.6291	Remote Similarity	NPD6273	Approved
0.6288	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6832	Phase 2
0.6284	Remote Similarity	NPD7487	Discontinued
0.6284	Remote Similarity	NPD4628	Phase 3
0.6284	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD1566	Phase 3
0.6281	Remote Similarity	NPD1564	Approved
0.6281	Remote Similarity	NPD1565	Approved
0.6276	Remote Similarity	NPD3748	Approved
0.6276	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD225	Approved
0.6273	Remote Similarity	NPD227	Approved
0.6271	Remote Similarity	NPD1239	Approved
0.6268	Remote Similarity	NPD7715	Approved
0.6268	Remote Similarity	NPD7714	Approved
0.6267	Remote Similarity	NPD7478	Approved
0.6267	Remote Similarity	NPD3950	Discontinued
0.626	Remote Similarity	NPD4766	Approved
0.626	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6049	Phase 2
0.625	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2067	Discontinued
0.625	Remote Similarity	NPD4094	Approved
0.6241	Remote Similarity	NPD6039	Approved
0.6241	Remote Similarity	NPD6065	Approved
0.6233	Remote Similarity	NPD5405	Approved
0.6233	Remote Similarity	NPD5406	Approved
0.6233	Remote Similarity	NPD5404	Approved
0.6233	Remote Similarity	NPD5408	Approved
0.6224	Remote Similarity	NPD4307	Phase 2
0.621	Remote Similarity	NPD2196	Discontinued
0.621	Remote Similarity	NPD6024	Approved
0.621	Remote Similarity	NPD2171	Approved
0.621	Remote Similarity	NPD6027	Approved
0.6207	Remote Similarity	NPD4793	Discontinued
0.6207	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD3764	Approved
0.6187	Remote Similarity	NPD3266	Approved
0.6187	Remote Similarity	NPD3267	Approved
0.6183	Remote Similarity	NPD1241	Discontinued
0.6183	Remote Similarity	NPD2652	Approved
0.6183	Remote Similarity	NPD2650	Approved
0.6169	Remote Similarity	NPD3226	Approved
0.6165	Remote Similarity	NPD4574	Approved
0.6165	Remote Similarity	NPD4576	Approved
0.6164	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD7305	Phase 1
0.6159	Remote Similarity	NPD7390	Discontinued
0.6154	Remote Similarity	NPD6663	Approved
0.6154	Remote Similarity	NPD8434	Phase 2
0.6148	Remote Similarity	NPD4657	Approved
0.6148	Remote Similarity	NPD1651	Approved
0.6148	Remote Similarity	NPD4655	Approved
0.6145	Remote Similarity	NPD8368	Discontinued
0.6144	Remote Similarity	NPD7606	Phase 3
0.6143	Remote Similarity	NPD4980	Approved
0.6142	Remote Similarity	NPD6685	Approved
0.6138	Remote Similarity	NPD6651	Approved
0.6136	Remote Similarity	NPD1711	Phase 2
0.6133	Remote Similarity	NPD2309	Approved
0.6133	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD7437	Approved
0.6131	Remote Similarity	NPD7436	Approved
0.6129	Remote Similarity	NPD4380	Phase 2
0.6129	Remote Similarity	NPD6585	Discontinued
0.6129	Remote Similarity	NPD6599	Discontinued
0.6125	Remote Similarity	NPD5494	Approved
0.6124	Remote Similarity	NPD1752	Approved
0.6124	Remote Similarity	NPD1756	Approved
0.6121	Remote Similarity	NPD9259	Approved
0.6121	Remote Similarity	NPD9257	Approved
0.6118	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD2607	Approved
0.6107	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD7082	Approved
0.6107	Remote Similarity	NPD2800	Approved
0.6106	Remote Similarity	NPD226	Approved
0.6103	Remote Similarity	NPD17	Approved
0.6103	Remote Similarity	NPD4199	Phase 3
0.6099	Remote Similarity	NPD5736	Approved
0.609	Remote Similarity	NPD4198	Discontinued
0.609	Remote Similarity	NPD7411	Suspended
0.6084	Remote Similarity	NPD3268	Approved
0.6074	Remote Similarity	NPD7741	Discontinued
0.6071	Remote Similarity	NPD9490	Approved
0.6067	Remote Similarity	NPD3750	Approved
0.6067	Remote Similarity	NPD7259	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data